- METHOD AND REAGENT FOR DEOXYFLUORINATION
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A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.
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Paragraph 0148-0150; 0152; 0154
(2021/05/29)
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- Nickel-Catalyzed Difluoromethylation of Arylboronic Acids with Bromodifluoromethane
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Although bromodifluoromethane (BrCF2H) is a simple and readily available fluorine source, direct formation of difluoromethylated arenes with BrCF2H has not been reported. Herein, we describe an efficient method to access difluoromethylated arenes through a nickel-catalyzed difluoromethylation of arylboronic acids with BrCF2H. The reaction exhibits high efficiency, good functional group tolerance and broad substrate scope, thus providing an efficient route for applications in drug discovery and development. Preliminary mechanistic studies reveal that a difluoromethyl radical is involved in the reaction.
- Fu, Xia-Ping,Xiao, Yu-Lan,Zhang, Xingang
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supporting information
p. 143 - 146
(2018/01/05)
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- Synthesis and evaluation of general mechanism-based inhibitors of sulfatases based on (difluoro)methyl phenyl sulfate and cyclic phenyl sulfamate motifs
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Several model mechanism-based inhibitors (MbIs) were designed and evaluated for their ability to inhibit sulfatases. The MbI motifs were based on simple aromatic sulfates, which are known to be commonly accepted substrates across this highly conserved enzyme class, so that they might be generally useful for sulfatase labeling studies. (Difluoro)methyl phenol sulfate analogs, constructed to release a reactive quinone methide trap, were not capable of irreversibly inactivating the sulfatase active site. On the other hand, the cyclic sulfamates (CySAs) demonstrated inhibition profiles consistent with an active site-directed mode of action. These molecules represent a novel scaffold for labeling sulfatases and for probing their catalytic mechanism.
- Hanson, Sarah R.,Whalen, Lisa J.,Wong, Chi-Huey
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p. 8386 - 8395
(2008/02/05)
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- Nucleophilic trifluoromethylation and difluorination of substituted aromatic aldehydes with Ruppert's and Deoxofluor? reagents
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Efficient, high yield syntheses of 2,2,2-trifluoro-1-(N,N-dialkylaminophenyl)-ethanols (3a, b) and 2,2,2-trifluoro-1-(hydroxyaryl)ethanols (6c-g) by reacting Ruppert's reagent, (trifluoromethyl)trimethylsilane (TMSCF3), with appropriate substra
- Singh, Rajendra P.,Chakraborty, Debashis,Shreeve, Jean'Ne M.
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p. 153 - 160
(2007/10/03)
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